Ionic multiresonant thermally activated delayed fluorescence emitters for light emitting electrochemical cells

Merve Karaman,
Abhishek Kumar Gupta,
Subeesh Madayanad Suresh,
Tomas Matulaitis,
Lorenzo Mardegan,
Daniel Tordera,
Henk J. Bolink,
Sen Wu,
Stuart Warriner,
Ifor D. Samuel and
Eli Zysman-Colman

Full Research Paper
Published 22 Sep 2022

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1. Graphical Abstract
2. Figure 1: Chemical structures of (a) reported ionic TADF emitters for LEECs, (b) the MR-TADF emitter DiKTa an...
  
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3. Scheme 1: Synthesis of DiKTa-OBuIm and DiKTa-DPA-OBuIm.
  
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4. Figure 2: (a) HOMO and LUMO electron density distribution and orbital energies of DiKTa-OMe and DiKTa-DPA-OMe...
  
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5. Figure 3: (a) Cyclic and differential pulse voltammograms measured in degassed MeCN with 0.1 M [n-Bu₄N]PF₆ as...
  
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6. Figure 4: (a) Steady-state emission spectra of DiKTa-OBuIm and DiKTa-DPA-OBuIm in 1 wt % doped mCP films, λ_ex...
  
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7. Figure 5: (a) Electroluminescence spectra of DiKTa-OBuIm (green curve), DiKTa-DPA-OBuIm (red curve) and 1% of ...
  
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Beilstein J. Org. Chem. 2022, 18, 1311–1321, doi:10.3762/bjoc.18.136

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Effect of a twin-emitter design strategy on a previously reported thermally activated delayed fluorescence organic light-emitting diode

Ettore Crovini,
Zhen Zhang,
Yu Kusakabe,
Yongxia Ren,
Yoshimasa Wada,
Bilal A. Naqvi,
Prakhar Sahay,
Tomas Matulaitis,
Stefan Diesing,
Ifor D. W. Samuel,
Wolfgang Brütting,
Katsuaki Suzuki,
Hironori Kaji,
Stefan Bräse and
Eli Zysman-Colman

Full Research Paper
Published 08 Dec 2021

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1. Graphical Abstract
2. Figure 1: Molecular structures of emitters.
  
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3. Figure 2: a) Molecular structure and b) optimized DFT-calculated geometry of DICzTRZ. Hydrogen atoms are omit...
  
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4. Figure 3: HOMO, HOMO–1 (H–1), LUMO, and LUMO+1 (L+1) electron density distributions (isovalue: 0.02) and ener...
  
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5. Figure 4: a) Cyclic voltammetry (CV) and differential pulse voltammetry (DPV) of DICzTRZ in DCM (scan rate = ...
  
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6. Figure 5: a) Prompt and b) delayed time-resolved decay in spin-coated 20 wt % CzSi film of DICzTRZ (λ_exc = 37...
  
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7. Figure 6: Angle-resolved photoluminescence measurement of a solution-processed film of 20 wt % DICzTRZ in CzS...
  
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8. Figure 7: Device characteristics of 20 and 30 wt % DICzTRZ-based OLEDs, which are represented by red and blue...
  
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9. Figure 8: Device efficiency simulation of the fabricated OLEDs depicting the variation in EQE with varied PL ...
  
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Beilstein J. Org. Chem. 2021, 17, 2894–2905, doi:10.3762/bjoc.17.197

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Exploring the possibility of using fluorine-involved non-conjugated electron-withdrawing groups for thermally activated delayed fluorescence emitters by TD-DFT calculation

Dongyang Chen and
Eli Zysman-Colman

Full Research Paper
Published 21 Jan 2021

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1. Graphical Abstract
2. Figure 1: Molecular structures of emitters discussed in this work.
  
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3. Figure 2: a) Calculated HOMO, LUMO, S₁ and T₁ energies, as well as HOMO and LUMO topologies of PhCF₃, PhOCF₃, ...
  
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4. Figure 3: Calculated HOMO, LUMO, S₁ and T₁ energies, as well as HOMO and LUMO topologies of 2CzCF₃, 2CzOCF₃, ...
  
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5. Figure 4: Calculated HOMO, LUMO, S₁ and T₁ energies, as well as HOMO and LUMO topologies of 2CzBN, 2CzTRZ, an...
  
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6. Figure 5: HOMO and LUMO distribution, HONTO and LUNTO of lowest singlet (S₁) and triplet excited (T₁) states ...
  
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7. Figure 6: HOMO and LUMO distribution, HONTO and LUNTO of lowest singlet (S₁) and triplet excited (T₁) states ...
  
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8. Figure 7: Calculated HOMO, LUMO, S₁ and T₁ energies, as well as HOMO and LUMO topologies of 5CzCF₃, 5CzOCF₃, ...
  
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9. Figure 8: Calculated HOMO, LUMO, S₁ and T₁ energies, as well as HOMO and LUMO topologies of 5CzBN, 5CzTRZ, an...
  
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10. Figure 9: HOMO and LUMO distribution, HONTO and LUNTO of lowest singlet (S₁) and triplet excited (T₁) states ...
  
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11. Figure 10: HOMO and LUMO distribution, HONTO and LUNTO of lowest singlet (S₁) and triplet excited (T₁) states ...
  
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12. Figure 11: HONTOs and LUNTOs of 2CzCF₃ in higher excited states (isovalue = 0.02).
  
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13. Figure 12: HONTOs and LUNTOs of 5CzCF₃ in higher excited states (isovalue = 0.02).
  
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Beilstein J. Org. Chem. 2021, 17, 210–223, doi:10.3762/bjoc.17.21

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Recent developments in enantioselective photocatalysis

Callum Prentice,
James Morrisson,
Andrew D. Smith and
Eli Zysman-Colman

Review
Published 29 Sep 2020

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1. Graphical Abstract
2. Scheme 1: Amine/photoredox-catalysed α-alkylation of aldehydes with alkyl bromides bearing electron-withdrawi...
  
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3. Scheme 2: Amine/HAT/photoredox-catalysed α-functionalisation of aldehydes using alkenes.
  
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4. Scheme 3: Amine/cobalt/photoredox-catalysed α-functionalisation of ketones and THIQs.
  
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5. Scheme 4: Amine/photoredox-catalysed α-functionalisation of aldehydes or ketones with imines. (a) Using keton...
  
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6. Scheme 5: Bifunctional amine/photoredox-catalysed enantioselective α-functionalisation of aldehydes.
  
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7. Scheme 6: Bifunctional amine/photoredox-catalysed α-functionalisation of aldehydes using amine catalysts via ...
  
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8. Scheme 7: Amine/photoredox-catalysed RCA of iminium ion intermediates. (a) Synthesis of quaternary stereocent...
  
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9. Scheme 8: Bifunctional amine/photoredox-catalysed RCA of enones in a radical chain reaction initiated by an i...
  
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10. Scheme 9: Bifunctional amine/photoredox-catalysed RCA reactions of iminium ions with different radical precur...
  
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11. Scheme 10: Bifunctional amine/photoredox-catalysed radical cascade reactions between enones and alkenes with a...
  
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12. Scheme 11: Amine/photocatalysed photocycloadditions of iminium ion intermediates. (a) External photocatalyst u...
  
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13. Scheme 12: Amine/photoredox-catalysed addition of acrolein (94) to iminium ions.
  
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14. Scheme 13: Dual NHC/photoredox-catalysed acylation of THIQs.
  
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15. Scheme 14: NHC/photocatalysed spirocyclisation via photoisomerisation of an extended Breslow intermediate.
  
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16. Scheme 15: CPA/photoredox-catalysed aza-pinacol cyclisation.
  
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17. Scheme 16: CPA/photoredox-catalysed Minisci-type reaction between azaarenes and α-amino radicals.
  
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18. Scheme 17: CPA/photoredox-catalysed radical additions to azaarenes. (a) α-Amino radical or ketyl radical addit...
  
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19. Scheme 18: CPA/photoredox-catalysed reduction of azaarene-derived substrates. (a) Reduction of ketones. (b) Ex...
  
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20. Scheme 19: CPA/photoredox-catalysed radical coupling reactions of α-amino radicals with α-carbonyl radicals. (...
  
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21. Scheme 20: CPA/photoredox-catalysed Povarov reaction.
  
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22. Scheme 21: CPA/photoredox-catalysed reactions with imines. (a) Decarboxylative imine generation followed by Po...
  
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23. Scheme 22: Bifunctional CPA/photocatalysed [2 + 2] photocycloadditions.
  
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24. Scheme 23: PTC/photocatalysed oxygenation of 1-indanone-derived β-keto esters.
  
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25. Scheme 24: PTC/photoredox-catalysed perfluoroalkylation of 1-indanone-derived β-keto esters via a radical chai...
  
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26. Scheme 25: Bifunctional hydrogen bonding/photocatalysed intramolecular [2 + 2] photocycloadditions of quinolon...
  
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27. Scheme 26: Bifunctional hydrogen bonding/photocatalysed intramolecular RCA cyclisation of a quinolone.
  
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28. Scheme 27: Bifunctional hydrogen bonding/photocatalysed intramolecular [2 + 2] photocycloadditions of quinolon...
  
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29. Scheme 28: Bifunctional hydrogen bonding/photocatalysed [2 + 2] photocycloaddition reactions. (a) First use of...
  
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30. Scheme 29: Bifunctional hydrogen bonding/photocatalysed deracemisation of allenes.
  
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31. Scheme 30: Bifunctional hydrogen bonding/photocatalysed deracemisation reactions. (a) Deracemisation of sulfox...
  
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32. Scheme 31: Bifunctional hydrogen bonding/photocatalysed intramolecular [2 + 2] photocycloaddition of coumarins....
  
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33. Scheme 32: Bifunctional hydrogen bonding/photocatalysed [2 + 2] photocycloadditions of quinolones. (a) Intramo...
  
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34. Scheme 33: Hydrogen bonding/photocatalysed formal arylation of benzofuranones.
  
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35. Scheme 34: Hydrogen bonding/photoredox-catalysed dehalogenative protonation of α,α-chlorofluoro ketones.
  
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36. Scheme 35: Hydrogen bonding/photoredox-catalysed reductions. (a) Reduction of 1,2-diketones. (b) Reduction of ...
  
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37. Scheme 36: Hydrogen bonding/HAT/photocatalysed deracemisation of cyclic ureas.
  
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38. Scheme 37: Hydrogen bonding/HAT/photoredox-catalysed synthesis of cyclic sulfonamides.
  
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39. Scheme 38: Hydrogen bonding/photoredox-catalysed reaction between imines and indoles.
  
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40. Scheme 39: Chiral cation/photoredox-catalysed radical coupling of two α-amino radicals.
  
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41. Scheme 40: Chiral phosphate/photoredox-catalysed hydroetherfication of alkenols.
  
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42. Scheme 41: Chiral phosphate/photoredox-catalysed synthesis of pyrroloindolines.
  
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43. Scheme 42: Chiral anion/photoredox-catalysed radical cation Diels–Alder reaction.
  
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44. Scheme 43: Lewis acid/photoredox-catalysed cycloadditions of carbonyls. (a) Formal [2 + 2] cycloaddition of en...
  
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45. Scheme 44: Lewis acid/photoredox-catalysed RCA reaction using a scandium Lewis acid between α-amino radicals a...
  
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46. Scheme 45: Lewis acid/photoredox-catalysed RCA reaction using a copper Lewis acid between α-amino radicals and...
  
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47. Scheme 46: Lewis acid/photoredox-catalysed synthesis of 1,2-amino alcohols from aldehydes and nitrones using a...
  
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48. Scheme 47: Lewis acid/photocatalysed [2 + 2] photocycloadditions of enones and alkenes.
  
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49. Scheme 48: Meggers’s chiral-at-metal catalysts.
  
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50. Scheme 49: Lewis acid/photoredox-catalysed α-functionalisation of ketones with alkyl bromides bearing electron...
  
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51. Scheme 50: Bifunctional Lewis acid/photoredox-catalysed radical coupling reaction using α-chloroketones and α-...
  
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52. Scheme 51: Lewis acid/photocatalysed RCA of enones. (a) Using aldehydes as acyl radical precursors. (b) Other ...
  
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53. Scheme 52: Bifunctional Lewis acid/photocatalysis for a photocycloaddition of enones.
  
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54. Scheme 53: Lewis acid/photoredox-catalysed RCA reactions of enones using DHPs as radical precursors.
  
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55. Scheme 54: Lewis acid/photoredox-catalysed functionalisation of β-ketoesters. (a) Hydroxylation reaction catal...
  
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56. Scheme 55: Bifunctional copper-photocatalysed alkylation of imines.
  
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57. Scheme 56: Copper/photocatalysed alkylation of imines. (a) Bifunctional copper catalysis using α-silyl amines....
  
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58. Scheme 57: Bifunctional Lewis acid/photocatalysed intramolecular [2 + 2] photocycloaddition.
  
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59. Scheme 58: Bifunctional Lewis acid/photocatalysed [2 + 2] photocycloadditions (a) Intramolecular cycloaddition...
  
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60. Scheme 59: Bifunctional Lewis acid/photocatalysed rearrangement of 2,4-dieneones.
  
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61. Scheme 60: Lewis acid/photocatalysed [2 + 2] cycloadditions of cinnamate esters and styrenes.
  
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62. Scheme 61: Nickel/photoredox-catalysed arylation of α-amino acids using aryl bromides.
  
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63. Scheme 62: Nickel/photoredox catalysis. (a) Desymmetrisation of cyclic meso-anhydrides using benzyl trifluorob...
  
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64. Scheme 63: Nickel/photoredox catalysis for the acyl-carbamoylation of alkenes with aldehydes using TBADT as a ...
  
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65. Scheme 64: Bifunctional copper/photoredox-catalysed C–N coupling between α-chloro amides and carbazoles or ind...
  
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66. Scheme 65: Bifunctional copper/photoredox-catalysed difunctionalisation of alkenes with alkynes and alkyl or a...
  
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67. Scheme 66: Copper/photoredox-catalysed decarboxylative cyanation of benzyl phthalimide esters.
  
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68. Scheme 67: Copper/photoredox-catalysed cyanation reactions using TMSCN. (a) Propargylic cyanation (b) Ring ope...
  
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69. Scheme 68: Palladium/photoredox-catalysed allylic alkylation reactions. (a) Using alkyl DHPs as radical precur...
  
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70. Scheme 69: Manganese/photoredox-catalysed epoxidation of terminal alkenes.
  
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71. Scheme 70: Chromium/photoredox-catalysed allylation of aldehydes.
  
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72. Scheme 71: Enzyme/photoredox-catalysed dehalogenation of halolactones.
  
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73. Scheme 72: Enzyme/photoredox-catalysed dehalogenative cyclisation.
  
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74. Scheme 73: Enzyme/photoredox-catalysed reduction of cyclic imines.
  
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75. Scheme 74: Enzyme/photocatalysed enantioselective reduction of electron-deficient alkenes as mixtures of (E)/(Z...
  
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76. Scheme 75: Enzyme/photoredox catalysis. (a) Deacetoxylation of cyclic ketones. (b) Reduction of heteroaromatic...
  
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77. Scheme 76: Enzyme/photoredox-catalysed synthesis of indole-3-ones from 2-arylindoles.
  
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78. Scheme 77: Enzyme/HAT/photoredox catalysis for the DKR of primary amines.
  
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79. Scheme 78: Bifunctional enzyme/photoredox-catalysed benzylic C–H hydroxylation of trifluoromethylated arenes.
  
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Beilstein J. Org. Chem. 2020, 16, 2363–2441, doi:10.3762/bjoc.16.197

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Synthesis and optoelectronic properties of benzoquinone-based donor–acceptor compounds

Daniel R. Sutherland,
Nidhi Sharma,
Georgina M. Rosair,
Ifor D. W. Samuel,
Ai-Lan Lee and
Eli Zysman-Colman

Full Research Paper
Published 04 Dec 2019

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1. Graphical Abstract
2. Scheme 1: Mild and direct C–H monofunctionalization of BQ 1: previous [14] and this work.
  
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3. Figure 1: Benzoquinone derivatives synthesized for this study, with the donor in red and the benzoquinone acc...
  
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4. Scheme 2: Synthesis of 2–4 via mild and direct C–H monofunctionalization of BQ (1).
  
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5. Scheme 3: Synthesis of 5 via double Suzuki coupling.
  
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6. Figure 2: Crystal structures of 3 and 4.
  
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7. Figure 3: HOMO/LUMO and S₁/T₁ energies as well as HOMO/LUMO electron density distribution profiles of 2–5.
  
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8. Figure 4: Cyclic voltammograms and differential pulse voltammograms of 2–5 in degassed DCM (scan rate = 100 m...
  
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9. Figure 5: UV–vis absorption spectra of 2–5 in DCM and photoluminescence spectrum of 3 in degassed DCM and in ...
  
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10. Figure 6: Time-resolved PL plots. a) Prompt decay and b) delayed decay curve of 3 in thin film (λ_exc = 378 nm...
  
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Beilstein J. Org. Chem. 2019, 15, 2914–2921, doi:10.3762/bjoc.15.285

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Recent advances in materials for organic light emitting diodes

Eli Zysman-Colman

Editorial
Published 27 Jul 2018

Beilstein J. Org. Chem. 2018, 14, 1944–1945, doi:10.3762/bjoc.14.168

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Copper-catalyzed asymmetric sp³ C–H arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalyst

Pierre Querard,
Inna Perepichka,
Eli Zysman-Colman and
Chao-Jun Li

Full Research Paper
Published 06 Dec 2016

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1. Graphical Abstract
2. Scheme 1: Design light-mediated arylation of THIQs.
  
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3. Figure 1: Reaction scope. Reaction conditions: THIQs (0.10 mmol), arylboronic acid (0.30 mmol), TBHP (0.2 mmo...
  
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4. Scheme 2: Evaluation of chiral ligands.
  
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5. Scheme 3: Proposed reaction mechanism.
  
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Beilstein J. Org. Chem. 2016, 12, 2636–2643, doi:10.3762/bjoc.12.260

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Ionic multiresonant thermally activated delayed fluorescence emitters for light emitting electrochemical cells

Effect of a twin-emitter design strategy on a previously reported thermally activated delayed fluorescence organic light-emitting diode

Exploring the possibility of using fluorine-involved non-conjugated electron-withdrawing groups for thermally activated delayed fluorescence emitters by TD-DFT calculation

Recent developments in enantioselective photocatalysis

Synthesis and optoelectronic properties of benzoquinone-based donor–acceptor compounds

Recent advances in materials for organic light emitting diodes

Copper-catalyzed asymmetric sp³ C–H arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalyst

Other Beilstein-Institut Open Science Activities

Keep Informed

Ionic multiresonant thermally activated delayed fluorescence emitters for light emitting electrochemical cells

Effect of a twin-emitter design strategy on a previously reported thermally activated delayed fluorescence organic light-emitting diode

Exploring the possibility of using fluorine-involved non-conjugated electron-withdrawing groups for thermally activated delayed fluorescence emitters by TD-DFT calculation

Recent developments in enantioselective photocatalysis

Synthesis and optoelectronic properties of benzoquinone-based donor–acceptor compounds

Recent advances in materials for organic light emitting diodes

Copper-catalyzed asymmetric sp3 C–H arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalyst

Other Beilstein-Institut Open Science Activities

Keep Informed

Copper-catalyzed asymmetric sp³ C–H arylation of tetrahydroisoquinoline mediated by a visible light photoredox catalyst